There are no hard and fast rules on anal training – every ass, every man and every situation is different. The best you can do is listen to your body and make informed choices for your own training.

I have had good experience with many different men, but I am in no way an authority. I am not a medical practitioner. The information I’m providing is from my own learning and practice with male subs. This is just a guide to inspire you on your journey of training your own ass. There are also many other guides here on Fetlife that I advise you to seek out and add to your anal training repertoire.

General Safety

You are ultimately responsible for your own self. Even if you have a Dom/me who you trust, your body is yours to live with for the rest of your life. You’ll never have another. Treat it well.

The ass is amazing. It has the capacity to expand enough to take a baby watermelon, no joke. Anal training must be done safely for the future health of your ass. The sphincter is a muscle, and just like any muscle, it takes perseverance, time and care to train your ass to the stage you want without damage. I have a double fisting slut and he has taken six years to get where he is. He takes great care of himself and he knows his limitations. This makes me, as a Domme, confident in our extreme play.

And because the sphincter is a muscle, when you stop training, your ass can return to the limited capacity you started out with. I’ve known a few subs who used to be anal sluts in their early twenties, stopped until their forties, and had to retrain their ass all over again like a virgin.

On every step of your journey, you need to monitor how your body is coping with anal training and play.

I’ve mentioned anal rinsing and hygiene in more detail below.

It goes without saying but… Don’t use sharp objects or anything that could pierce or graze the walls of your ass. Abrasions or lacerations can cause infection and enable bacteria to get into the bloodstream.

Sometimes your ass can get spent from overuse or from a heavy pounding. It is important that you rest your ass for days, even weeks, if you are into the heavy stuff. During or in between play, if you notice anything out of the ordinary, bad pain, blood or other discharge: STOP! It can be a sign that something is wrong. You might need to rest your ass for a good month, or even see a doctor.

I want to make this clear: It is ok to only want to go to a certain size – it’s not about all or nothing. The key is to work with your body. Don’t force, just feel. And luuuuube!

When training and playing with a partner:

Never be afraid to ask for more lube, to change positions, rhythm or toy, or even stop if you need to. If you feel you can’t ask, or use your safe word, you’re with the wrong partner/Domme.

I always encourage my subs to invest in their own toys. It is best not to share. If toys are shared, make sure they are thoroughly washed with the appropriate solution. Use condoms as a cover when necessary. Likewise with gloves, and change them regularly to avoid cross contamination.

Please remember that anal sex increases the chances of contracting STDs and other sexual viruses, so using protection is smart. If you have many play partners, you and your anal partner should be getting sexual screening tests every three months, even if you use protection. And it is wise for monogamous players to do the same. I would be wary of anyone who hesitates. Be aware that in general hard diseases like HIV can take nine months so show up on test results. I’m not saying don’t trust your partner, I’m saying be responsible. Responsible is sexy!

Before You Start

Lubrication

At first you can use a gentle water-based lube for basic play. When partner play will include mouth-to-ass then an organic lube such as coconut oil is good, especially for taste. However, oil based lubes are known to compromise the integrity of condoms, so consider this. If you get into the extreme side of anal play, fisting etc, then I’d suggest switching to a silicon-based lube, or something like J-Lube or a hybrid like Fist by MR B. Again, be aware that some lubes compromise the integrity of condoms. Make sure your condoms and lube are compatible!! And lubricants with sugar in them (ingredients that end in -ose) are not good for vaginal use as they compromise pH levels and bacterial flora.

Douching

Anal douching is rinsing out the rectum to ready it for penetration.

When playing with yourself it is generally not necessary to douche. If you are worried about hygiene you can always use condoms on your toys and basic medical gloves for cleanliness. If you use your toys without protection, wash them afterwards with a toy specific cleaning solution.

Douching is always expected when you intend to have anal play with a partner!!! – it’s respectful and hygienic. However, I recommend you don’t douche too often because it can wash out the good bacteria from your anal passage that keeps your ass protected. So, it’s good to plan your anal play with partners so you can regulate your douching and rest your body.

There are two main ways to rinse:

• For a regular rinsing you can use a simple rectum douche applicator that you can buy from your local chemist that flushes the basic area. I find this is all that is needed for basic anal play. After a bowel movement, a thorough douche a few hours before play is generally all that is required. Follow the instructions on the applicator box. Make sure the applicator is full of water so you don’t fill your ass with air. And repeat the process until the water runs clear. Then it is always good to do another quick douche an hour to 30mins before play.
• For hardcore rinsing you can flush out the whole bowel using an enema kit, which you can also buy at a chemist. This is an aggressive flushing of the bowel and is good for extreme play or if you are a porn star. Don’t do this too often otherwise you can compromise the safety of your bowel leaving you more exposed to infection and disease.

You are the best judge of what your body can handle, which method and how often. It is a very good idea to practice rinsing techniques before you have signed up to play with anyone. You don’t want to be rushing to the store and trying to work out how to use the applicators the day of your play.

Shaving

You don’t need to shave to do anal. Shaving is just for visual aesthetics. If someone says it’s ‘cleaner’, its their belief not fact. Shaving actually attracts bad bacteria and increases the risk of STDs and other diseases. It creates microscopic wounds and draws fluids to the area such as blood, puss and mucus for healing, and your skin has to cope with ingrown hairs, zits, cysts, rashes, abrasions and extra sweat. Yes indeedy. All this can be avoided by not shaving.

Personally, I don’t think a woman should tell a man what to do with his own body. My ethical beliefs carry through to my Domming. It is because I don’t play a role – being a Domme is an extension of who I am. I say to all my subs, “Do whatever makes you feel comfortable, confident and sexy”. That’s what I want.

Really, it’s the man that turns me on, not whether he is bare or naturale.

Toys

Play with different toys is part of the fun of anal training. Butt plugs, dildos, vibrators, beads and pumps are usual items in the anal player’s arsenal. Different asses enjoy different sensations, and you can only know by trying each toy. Some people like their ass being widened, some like being penetrated to the base, others prefer rim play and most enjoy prostate stimulation – there is a toy for everything. Firmly deciding what you like before trying can limit your experience. I suggest being open to all prospects, try everything, you might surprise yourself.

The typical toys:

• Butt plugs – widen the cavity. Some are designed heavy, putting pressure on the inside of the rim or against the prostate. They are also used for decoration with tails and diamontes, etc.
• Beads – fill the cavity but are generally designed for rim stimulation especially when being pulled out.
• Pumps – go in deflated as not to stress the rim and then are pumped up inside the cavity to create a feeling of fullness.
• Dildos – are used primarily for movement sensation and to simulate a cock.
• Vibrators – provide a gentle hum. They can target areas such as the rim or prostate. They are usually in the shape of a cock and can be used like a dildo.
• Fingers – Yes, that’s right, fingers are the first anal toys ever made. They are organic, easy to clean and have many functions. However, they are always underestimated. Ideally, they should be the first toy to explore with. You have full control over them and can feel your way so you can treat yourself carefully.

Obviously, it is best to start off small and then up-size when your ass is ready, but don’t think bigger is better. There is no one size fits all. Toys come in different materials – steel, glass, rubber, plastic… – and give different effects. However, I would suggest using the toys that have a soft rubber coating first for beginners, and toys that are smooth to limit rim stress.

For the adventurous, (and when you have the hang of anal play) some toys can even be household products or organic, such as a cucumber (but it’s a good idea to cover them with a condom).

There is so much fun to be had! If you really get into the art of anal, pretty soon you’ll see everything as a potential anal toy.

Essentials for your anal kit:

• Lube – Choose the right one for your body, your equipment and the job at hand. Test them first. There is nothing worse than using lube that dries out or gets tacky. Certain lubes can make or break an experience. I suggest a good quality water-based lube for basic beginner play, and something hybrid such as Fist by Mr B or even J-Lube for the hardcore stuff.
• Condoms – are important when you share your training with a partner but they can also be used for safety such as holding onto smaller toys or organic toys that can get too adventurous for easy retrieval.
• Gloves – keep things clean and are good when training with partners. I find a lot of times condoms break when I take them off my peg, so gloves are very convenient. They can also be cut up and used as dental dams for protective rimming and pussy licking.
• Wet wipes – are handy all round to clean up spills, dribbles and wayward lube. And just as gloves, they are good to help take off condoms from toys.
• Towel – for a drop sheet. It catches any spills, dribbles and wayward lube, and is an easy way to protect and clean up the space.

Non-essentials:

• Pillows – help you to prop up your ass for easy access and relaxes the lower back.
• A wall mirror – is good so you can see what’s happening in terms of angles and depths. Plus it’s sexy and fun to watch.
• Yoga – is something I suggest to all my boys if they are particularly stiff and serious about their anal play. Being flexible enables you to have more control training yourself and it means that you can more easily experiment in different positions, especially when someone is pegging you. If you don’t want to do yoga, try other sports stretches. One major goal would be to touch your toes.
• Cock rings – add a little something extra to an experience. For most beginners their cocks go flaccid when their ass is penetrated so cock rings can help you stay hard if you need to.

When you have your first anal play / pegging session with a Domme bring your toys to add to the play cache. I had a fantastic sub who brought his own latex opera gloves for me to use. Perfect for fisting.

Steps for Anal Training

I suggest you play on your own first without a partner until you feel comfortable. The pace of progression is entirely up to you and your ass. I would suggest to concentrate on ass play at least once a week at first until your ass builds up some stamina. It’s best to judge on how well your ass is handling the training. There is no rush, you want to enjoy this. If your play becomes rougher or more extreme, you will likely have to take longer breaks between so your ass has the time to recoup. All in moderation.

Sometimes it can take a little while for your body to like anal play. It is about training both physically and mentally. Some people can feel a little queasy at the beginning especially when using a long toy for the first time, but that’s no problem, it’s normal. It usually doesn’t last. But once you’ve got the need, you’ll likely be aching for it and your sexual experiences will become more incredible. However, if anal is not for you, don’t be disappointed. You may have all the intentions in the world to become an anal slut, but just sometimes it doesn’t work out. You haven’t failed, you have just learnt something new about yourself.

It’s important to note that for most, especially beginners, when the ass is penetrated, the cock usually becomes flaccid. It is the body’s natural reaction. My guess is that the brain finds it hard to focus on two sensations at once, just like how the brain can’t focus on two points of pain at the same time – it switches between the two. So, you might start with a hard-on ready for anal but as soon as your ass is penetrated you’ll likely go flaccid. That’s perfectly normal. Some cocks go up and down like a yoyo, but very few keep a hard-on. However, streaming pre-cum, even when flaccid, is common. The majority, especially beginners, still need cock stimulation to get them to orgasm.

Fingering comes first

Have short nails, and use gloves if desired. Get yourself in a comfortable position, usually so you can curve your torso to easily reach your ass. A pillow under your lower back can help.

Before lubing up, place the tip of your finger on your puckered hole. I always do this to my subs as my first action. I want to feel the anus relax – some anal virgins naturally squeeze their ass especially when they feel cold lube but I want them to get use to my finger, to be comfortable before lube and before I enter. Practice relaxing your ass when your dry finger is against you.

Place lube both on the anus and around the finger. Find the anus inlet with the tip of your finger and then only push in to the first knuckle. Wait until the sphincter relaxes before going any further. This can take some time, and usually it is a mental process. Sometimes I stroke a sub’s back or ass to make him feel more relaxed, and also to divert attention. Avoid touching your cock as usually it will make you squeeze your ass – save this for later.

When it feels comfortable and the ass is relaxed, turn your finger to transfer lube and then continue to push the whole finger in slowly until it’s enough. Pull out and push in a few times. Re-lube when needed.

Try wiggling your finger, turning, thrusting, circling, pushing – experiment and find out what feels good for you.

When one finger can be easily taken, try two, then three… re-lube as necessary. Again, with each new finger addition explore what sensations are good for you.

This process can take three or four sessions. There’s no rush. It is most important you listen to your body without other distractions for the first few times. Then when you are acquainted with your ass, you can put on some porn and jerk off while you play, have some fun in the shower, or have some naughty time with a partner.

And… if you like fingers in your ass, this could be the start of you enjoying fisting.

Prostate stimulation

Every guy is designed differently. Some prostates are easy to find as they protrude while others feel no different from the internal wall. Some are positioned shallow and some are deep. And sometimes the g-spot isn’t actually on the prostrate but above or below. The best way is trial and error and when you are with a partner, guide them.

But all prostates are positioned towards the cock. To find it, slip one lubed finger into your ass so the pad is facing you – go in from the front. The prostate most often feels like a little soft hump about a finger in, but find the area that gives you the most pleasure… and lock it to memory. Try finding it again. When you feel the sweet spot play with different stimulation techniques – the come-hither, tapping, thrusting, circling, pushing… Discover what you like and what your body reacts to, which can be two different things. Remember so you can share the info with your partner.

Prostate stimulation can be key to an assgasm but it isn’t the Holy Grail. I’ve experienced a few subs coming just by getting my finger past the rim of their ass, I know that the mind has a lot of pull when assgasm is your goal.

Buttplug trainers

The first toy I would suggest to use is a small anal training butt plug. They are usually thinner than most regular butt plugs, are lighter with a bigger stopper and made with soft, flexible materials. You can buy anal training kits with three butt plugs online or at sex stores.

Choose the smallest first – you can use a condom for easy cleaning if you wish – and lube it up thoroughly. Push it in gently and leave it to sit in your anal passage for about ten minutes at the beginning. You can do this a few times over two weeks if you are particularly tight, increasing the length of time.

When you feel up for it you can take hold of the base and use it to thrust the plug in and out of your ass. And when you are comfortable with the plug, put on some porn and jerk off while you play. Keep it in when you have sex with a partner.

Upgrade to the next size when ready.

Pegging yourself

When you can successfully use the second size butt plug, next I would suggest moving on to a flexible jelly dildo with good base suction. Basically, the longer they are, the thicker they get. A 6’ is a good starter. Use a smooth dildo first with a small cock head as ribs and veins put more stress on the rim, as does a large cock head.

Before you use this dildo, you can use your familiar butt plug to open yourself up first. This helps the ass adjust and prepare, and by this stage might increase your arousal.

Thoroughly lube up the dildo, and you can always use a condom for easy cleaning. Lying on your back, knees bent to your chest is a good starting position to open and relax your ass. Slowly edge the dildo into your ass and rest with it to allow your ass to get used to the feel, fill and depth.

Find the depth point. Some might be able to take a dildo to the base and others might only be able to take it half way. Everyone is different and there are always other factors involved that can affect the tightness of your ass such as stress or tiredness, etc. So each time your depth or width capacity might be a little different. You can mark your depth capacity with your hand, using it as a stopper for when you thrust in.

When you’re ready, relaxed and lubed enough, slowly start sliding the dildo in and out. Play with speed, angle and depth, and play with your cock at the same time.

You might need a couple of sessions of dildo play to feel confident. When you’ve got the hang of it, start introducing other elements such as porn or different positions such as doggy or standing, which affect tightness.

The suction base of the dildo allows for hands free play. The easiest is to stick the dildo on the wall of your shower at the level of your ass and use the other wall to push back as leverage.

For a more advanced position, you can stick the dildo upright on a chair and use your legs and body weight to penetrate yourself, holding on to the chair. Or you can stick the dildo onto a tiled floor, though you have to be flexible and use physical execration to penetrate yourself. It will be tiring but that can also increase pleasure. You might want to stretch first. In fact, stretching is a good idea for any pegging.

Toys for fun and adventure

When you know your ass, introduce as many different toys as you can to your play regime. That is the only way you will know what you like and what works on your body. I’ve had a sub that went into a hyper-fit when I inserted a vibrator and another one who asked me, ‘Is it in yet’? So, everyone is different and the body can surprise you. What you imagine you might like may turn out to be just meh, and what you thought was a little silly could perhaps elicit the most earth-shattering orgasms for you.

Steel butt plugs are a fun addition to anal training. They are discrete enough to be used in public places. Some people like to watch TV with them, go do their shopping, or even go to work. This does take some training for anal endurance. Butt plugs are often used as a domination device. And I’ve heard that if you sleep with a butt plug in you will get the most amazing sexual dreams. I can’t confirm this, it is likely a myth, but a damn good one, I think.

Anal pumps create less stress on anal entry/exit and are a more gentle way to train the anal passage to stretch. They are inserted flat and then pumped up while in the ass. They are a favourite of nappy and mummification players as they can be inserted at the beginning of the scene and put into action at a later stage. I do know some subs who prefer this method of anal stimulation as they aren’t into the vigours of pegging but adore the feeling of being filled up.

Some people get a thrill out of using organic pegs such as cucumbers, carrots and celery. It is a fun way to add a cold element to anal play by freezing them, and some players even use icy poles or frozen tubes. I know of some people who use ginger to warm up the ass, but I’d say be very careful with this type of play as it chemically affects the ass’s ecosystem.

I’ve had one sub who enjoyed using candles. When his ass adjusted to the stretch of one, two, three… he’d keep adding more until he was satisfied.

Basically, mix it up and have fun.

Training with a Domme, even online

I don’t tend to train subs online, but I have done it a couples of times. I know it can be a very intimate experience. A sub shares his body with me, he trusts me, listens to me, does what I say. We discuss the feeling for him, how his body is reacting, what he thinks, what he desires… and all this before we see each other’s faces. Damn.

To train one particular sub for pegging, the most important thing was communication, honest and pure communication. He was very diligent, buying the toys I suggested, keeping track of our timetable, always reminding me how excited he was for the training session the next day.

We trained in real time, together. I required my sub to take pics and videos, that way I could see how his body was responding to my tasks and I could make the appropriate adjustments. When I can’t see what is happening, I’m training blind.

A lot of the training was based on Sherlock’s deduction method. I compiled my knowledge gained from other subs, and shaved it down to what I thought would best work for my sub according to his unique reactions.

There were two things that made the training successful:

• 1. I naturally cared for my sub, even though I had never met him.
• 2. We had a goal for him to be at a certain level – to get him to a stage where he could take a good pegging – for when we met. It meant the training was more vigorous as we had a time limit.

Training for Assgasms

I’d say assgasm is something a lot of players want to aim for. It is certainly spectacular to watch and feel (if you are the fister too). It is very common for people who assgasm to have multiples… several a minute. And also, to train a cock to explode with only ass stimulation can be incredible.

As a beginner, you want to enjoy what you can do first before training for the next stage. There’s no rush. But, I guess I’m going to have to write up another piece for assgasms, hey?

This is a work in progress. As I learn more I will be adding to and refining.